Decarboxylation of cinnamic acids by Saccharomyces cerevisiae

Gramatica, Paola; Ranzi, Bianca Maria; Manitto, Paolo

doi:10.1016/0045-2068(81)90039-0

Cited by 31 publications

(27 citation statements)

References 20 publications

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“…Goodey and Tubb (12) examined the generation of phenolic off-flavors by yeasts in beer and demonstrated ferulic acid decarboxylation to 4-vinylguaiacol mediated by the PAD1 gene (then named the POF1 gene) with lesser action on coumaric and cinnamic acids. However, the decarboxylation of ferulic and coumaric acids by S. cerevisiae in laboratory cultures has been reported by other authors (7,13,48) to be slow and with low activity, a suggestion that we confirm with a lack of activity detected by Pad1p on coumaric acid over 10 h.…”

Section: Discussionsupporting

confidence: 78%

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

Stratford

Plumridge

Archer

2007

Appl Environ Microbiol

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The spoilage yeast Saccharomyces cerevisiae degraded the food preservative sorbic acid (2,4-hexadienoic acid) to a volatile hydrocarbon, identified by gas chromatography mass spectrometry as 1,3-pentadiene. The gene responsible was identified as PAD1, previously associated with the decarboxylation of the aromatic carboxylic acids cinnamic acid, ferulic acid, and coumaric acid to styrene, 4-vinylguaiacol, and 4-vinylphenol, respectively. The loss of PAD1 resulted in the simultaneous loss of decarboxylation activity against both sorbic and cinnamic acids. Pad1p is therefore an unusual decarboxylase capable of accepting both aromatic and aliphatic carboxylic acids as substrates. All members of the Saccharomyces genus (sensu stricto) were found to decarboxylate both sorbic and cinnamic acids. PAD1 homologues and decarboxylation activity were found also in Candida albicans, Candida dubliniensis, Debaryomyces hansenii, and Pichia anomala. The decarboxylation of sorbic acid was assessed as a possible mechanism of resistance in spoilage yeasts. The decarboxylation of either sorbic or cinnamic acid was not detected for Zygosaccharomyces, Kazachstania (Saccharomyces sensu lato), Zygotorulaspora, or Torulaspora, the genera containing the most notorious spoilage yeasts. Scatter plots showed no correlation between the extent of sorbic acid decarboxylation and resistance to sorbic acid in spoilage yeasts. Inhibitory concentrations of sorbic acid were almost identical for S. cerevisiae wild-type and ⌬pad1 strains. We concluded that Pad1p-mediated sorbic acid decarboxylation did not constitute a significant mechanism of resistance to weak-acid preservatives by spoilage yeasts, even if the decarboxylation contributed to spoilage through the generation of unpleasant odors.

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Section: Discussionsupporting

confidence: 78%

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

Stratford

Plumridge

Archer

2007

Appl Environ Microbiol

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“…Accordingly, triCA3 (cis-2), diCA1 (3), diCA5 (7), and diCA7 (9) are stronger antioxidants than CA itself as shown by the inhibition ratio ( Table 4).…”

Section: The 3-methylenefuran-2(3h)-one Moiety Of 3 Was Unambiguouslymentioning

confidence: 93%

“…It is reasonable to assume that, of the CA radicals a -c, the mesomers b and c combine (! I(1)), followed by acid/base-catalyzed decarboxylation, driven by aromatization of the quinomethane part, to yield diCA5 (7). Then, the attack of the monomeric CA radical b on the ethenyl bond of 7, followed by MCP/H 2 O 2 catalysis, leads to I(2).…”

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confidence: 96%

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Biotransformation of p‐Coumaric Acid (=(2E)‐3‐(4‐Hydroxyphenyl)prop‐2‐enoic Acid) by Momordica charantia Peroxidase

Liu

Huang

Wan

et al. 2007

Helvetica Chimica Acta

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LC/MS3 -Guided biotransformation of p-coumaric acid (¼ (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid; CA) with H 2 O 2 /Momordica charantia peroxidase at pH 5.0 and 458 in the presence of acetone has resulted in the isolation of three CA trimers, triCA1 (1), triCA2 (trans-2), and triCA3 (cis-2), and seven CA dimers, diCA1 -diCA7, i.e., 3 -9, among which seven (triCA1 -triCA3 and diCA1 -diCA4) are new compounds and three (diCA5 -diCA7) are known compounds. The structures were established by 2D-NMR such as HSQC, HMBC, and NOESY measurements. The possible mechanism for the formation of the products is also discussed (Schemes 1 -3). This is the first time that the biotansformation of pcoumaric acid catalyzed by peroxidase in vitro was achieved. Compounds triCA3 (cis-2), diCA1 (3), diCA5 (7), and diCA7 (9) exhibit a stronger antioxidative activity than the parent CA.

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“…An (E)-configuration of the alkenic bond seems mandatory; the corresponding (Z)-stereoisomers were nonsubstrates in these reactions [444]. (E)-Cinnamaldehyde was decarbonylated and styrene was obtained as a product [445].…”

Section: C─c Bond-forming and Breaking Reactionsmentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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Decarboxylation of cinnamic acids by Saccharomyces cerevisiae

Cited by 31 publications

References 20 publications

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

Biotransformation of p‐Coumaric Acid (=(2E)‐3‐(4‐Hydroxyphenyl)prop‐2‐enoic Acid) by Momordica charantia Peroxidase

Yeast‐Mediated Stereoselective Synthesis

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